Were the OSCR CFO’s share sales discretionary or under a Rule 10b5-1 plan?

The CFO’s share sales were executed under a Rule 10b5‑1 instruction letter entered into on August 8, 2025. This pre‑arranged plan means the trades were scheduled in advance, reducing the significance of their timing as a signal of management’s short‑term outlook.

Oscar Health (OSCR) CFO’s planned share sale covers equity tax withholding

Filing Impact

(Very High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported open‑market sales of 31,683 shares of Class A Common Stock on June 2, 2026. The shares were sold in two transactions of 8,977 shares at $22.45 and 22,706 shares at $21.74 per share. A footnote states the sales were effected under a Rule 10b5‑1 instruction letter entered into on August 8, 2025 to satisfy the reporting person’s tax withholding obligations upon vesting of previously granted equity awards. The filing also notes 75,000 shares held indirectly by the MQB Irrevocable Trust.

Insights

CFO’s 31,683-share sale is pre-planned and tied to tax withholding.

The filing shows Oscar Health CFO Richard Scott Blackley sold 31,683 Class A shares on June 2, 2026 at weighted average prices of $21.74 and $22.45. Footnotes explain these sales were executed under a Rule 10b5‑1 instruction letter dated August 8, 2025.

The same footnote states the purpose was to cover the reporting person’s tax withholding obligation upon vesting of previously granted equity awards, making this a compensation-related liquidity event rather than a discretionary sale based on near-term outlook. The filing also records 75,000 shares held indirectly through the MQB Irrevocable Trust.

Because the transactions are both pre‑planned and tax‑driven, and the filing does not indicate unusually large reductions in overall holdings, this activity is generally interpreted as routine administration of equity compensation rather than a change in fundamental views on OSCR. Future company filings may further detail any additional equity awards or scheduled 10b5‑1 sales.

Insider Trade Summary 10b5-1

Net Seller: 31,683 shares ($695,162)

Net Sell 3 txns

Insider Blackley Richard Scott

Role Chief Financial Officer

Sold 31,683 shs ($695K)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	22,706	$21.74	$494K
Sale	Class A Common Stock	8,977	$22.45	$202K
holding	Class A Common Stock	--	--	--

Holdings After Transaction: Class A Common Stock — 1,083,954 shares (Direct, null); Class A Common Stock — 75,000 shares (Indirect, By MQB Irrevocable Trust)

Footnotes (1)

The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.03 to $22.02, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected. Includes shares to be issued in connection with the vesting of one or more restricted stock units. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.03 to $22.96, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

Key Figures

Shares sold total: 31,683 shares First sale size: 8,977 shares First sale price: $22.45 per share +4 more

7 metrics

Shares sold total 31,683 shares Net shares sold by CFO on June 2, 2026

First sale size 8,977 shares Open-market sale of Class A Common Stock

First sale price $22.45 per share Weighted average price for 8,977-share sale

Second sale size 22,706 shares Open-market sale of Class A Common Stock

Second sale price $21.74 per share Weighted average price for 22,706-share sale

10b5-1 plan date August 8, 2025 Date of Rule 10b5-1 instruction letter governing sales

Indirectly held shares 75,000 shares Class A shares held by MQB Irrevocable Trust

Key Terms

Rule 10b5-1 instruction letter, tax withholding obligation, weighted average price, restricted stock units, +1 more

5 terms

Rule 10b5-1 instruction letter regulatory

"The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025"

tax withholding obligation financial

"to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards"

weighted average price financial

"The price reported in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

restricted stock units financial

"Includes shares to be issued in connection with the vesting of one or more restricted stock units."

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

MQB Irrevocable Trust financial

"Class A Common Stock ... nature_of_ownership: By MQB Irrevocable Trust"

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google

Form 4 Insider Transactions: What Each Field Means →

06/04/2026 - 04:15 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Blackley Richard Scott

(Last)

(First)

(Middle)

75 VARICK STREET, 5TH FLOOR

(Street)

NEW YORK

10013

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Financial Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/02/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	06/02/2026		S		22,706⁽¹⁾	D	$21.74⁽²⁾	1,083,954⁽³⁾	D
Class A Common Stock	06/02/2026		S		8,977⁽¹⁾	D	$22.45⁽⁴⁾	1,074,977⁽³⁾	D
Class A Common Stock								75,000	I	By MQB Irrevocable Trust

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.03 to $22.02, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

3. Includes shares to be issued in connection with the vesting of one or more restricted stock units.

4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.03 to $22.96, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

Remarks:

	/s/ Melissa Curtin, Attorney-in-fact	06/04/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Oscar Health (OSCR) report for its CFO?

Oscar Health reported that CFO Richard Scott Blackley sold 31,683 shares of Class A Common Stock on June 2, 2026. The transactions were open‑market sales executed at weighted average prices of $21.74 and $22.45 per share, according to the Form 4 filing.

Why did Oscar Health’s CFO sell 31,683 OSCR shares?

The filing states the sales were made to satisfy the reporting person’s tax withholding obligation upon vesting of previously granted equity awards. This indicates the transactions are related to equity compensation and associated taxes rather than a standalone decision to reduce ownership.

At what prices did the Oscar Health CFO sell OSCR shares?

The Form 4 shows 8,977 shares sold at a weighted average price of $22.45 and 22,706 shares sold at a weighted average price of $21.74. Footnotes add that individual trades occurred in ranges between $21.03 and $22.96 per share.

Does the Oscar Health CFO hold any OSCR shares indirectly?

Yes. One entry identifies 75,000 shares of Class A Common Stock held indirectly by the MQB Irrevocable Trust. This is recorded as indirect ownership, separate from the CFO’s directly held shares, providing additional context on total reported holdings.

What does the Form 4 say about remaining holdings after the OSCR CFO’s sales?

Each transaction line reports a total number of shares following that transaction, indicating the CFO retained a substantial direct position after selling 31,683 shares. The filing does not describe any derivative positions, as the derivative summary section shows no remaining derivative securities.